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Issue 2, 2018
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Concise total synthesis of (+)-asperazine A and (+)-pestalazine B

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Abstract

The highly convergent total synthesis of dimeric diketopiperazine alkaloids (+)-asperazine A and (+)-pestalazine B is described. A critical aspect of our expedient route was the development of a directed regio- and diastereoselective C3–N1′ coupling of complex tetracyclic diketopiperazine components. This late-stage heterodimerization reaction was made possible by design of tetracyclic diketopiperazines that allow C3-carbocation coupling of the electrophilic component to the N1′ locus of the nucleophilic fragment. The application of this new coupling reaction to the first total synthesis of (+)-asperazine A led to our revision of the sign and magnitude of the optical rotation for the reported structure.

Graphical abstract: Concise total synthesis of (+)-asperazine A and (+)-pestalazine B

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Publication details

The article was received on 19 Oct 2017, accepted on 04 Dec 2017 and first published on 08 Dec 2017


Article type: Communication
DOI: 10.1039/C7OB02985C
Citation: Org. Biomol. Chem., 2018,16, 202-207
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    Concise total synthesis of (+)-asperazine A and (+)-pestalazine B

    B. M. Nelson, R. P. Loach, S. Schiesser and M. Movassaghi, Org. Biomol. Chem., 2018, 16, 202
    DOI: 10.1039/C7OB02985C

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